EP0648333A1 - Immobilized carbohydrate biosensor - Google Patents
Immobilized carbohydrate biosensorInfo
- Publication number
- EP0648333A1 EP0648333A1 EP94914654A EP94914654A EP0648333A1 EP 0648333 A1 EP0648333 A1 EP 0648333A1 EP 94914654 A EP94914654 A EP 94914654A EP 94914654 A EP94914654 A EP 94914654A EP 0648333 A1 EP0648333 A1 EP 0648333A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- biosensor
- carbohydrate
- derivative
- biosensor according
- bound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54366—Apparatus specially adapted for solid-phase testing
- G01N33/54373—Apparatus specially adapted for solid-phase testing involving physiochemical end-point determination, e.g. wave-guides, FETS, gratings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/805—Optical property
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/806—Electrical property or magnetic property
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/827—Lectins
Definitions
- the present invention relates to a biosensor in which a carbohydrate or a derivative thereof is used to generate a detectable signal via the specific binding of a protein, a virus or a cell.
- Biosensors are characterised by a physical or chemical signal transducer, which response is activated by a specific interaction between a biochemical structure (which directly or indirectly has been bound to the transducer) and one or several analytes.
- Biosensors are used to detect the analyte/analytes and in certain cases also for quantification of the analyte/analytes.
- biosensor has been made specific so that a general physical or chemical parameter (e.g. temperature, pH, optical density) can be used for the detection of one specific substance in a complex mixture of non-specific substances.
- a general physical or chemical parameter e.g. temperature, pH, optical density
- biosensor The limitations of the biosensor are the specificity of the biochemical structure bound to the transducer, the range of specificity and stability, and, that the transducer signal has to be made independent of the background changes in the parameter that the transducer is measuring.
- Methods of Enzymology, volume 137 several articles are describing different aspects of biosensors.
- Biosensor - physical or chemical signal transducer e.g. photometer, chemical electrode, temperature or pressure signal transducer, which directly or indirectly has been connected with a biochemical structure.
- an enzyme e.g. a specific protein or antibody
- the biosensors have been given the property of being able to detect substances which specifically bind to the biochemical structure in a qualitative or quantitative way.
- Reflection measurement - measurement of the intensity of light reflected from a surface where the properties of the surface influences the reflection, e.g. biomolecules which change the refraction index of the surface.
- Polarisation measurement - measurement of the polarisation of polarised light usually as the angle of polarisation, which is depending on the binding of biomolecules, virus or ceils.
- Ellipsometry optical physical measurement technique which can be used to measure small changes of refraction index at surfaces with high sensitivity, by measuring changes in elliptisity of polarised light, e.g. as caused by the presence of biomolecules on the surface.
- Piezoelectric crystal - crystal which frequency can be influenced by changes of mass or pressure which can be measured electrically, for example the change of mass caused by the presence of biomolecule(s), virus or cell(s) bound to the crystal surface.
- Electrochemical electrode - measuring device which generates an electrical signal caused by an electrochemical reaction at the electrode which is related to a chemical parameter, e.g. pH, p0 2 , pC0 2 , the values of which can vary because of the presence of analyte(s) in a sample specific for a compound bound to the measuring device.
- a chemical parameter e.g. pH, p0 2 , pC0 2
- Thermistor - electrical resistance device which changes resistance with the temperature; biochemical reactions are characterised by e.g. specific values of heat consumption/formation, which can be registered via the thermistor.
- the present invention describes a biosensor where this specificity is used for determination of such a component in a sample.
- the invention is characterised by that the carbohydrate or a derivative thereof is bound to a surface in the biosensor.
- carbohydrate As carbohydrate, one can use fragments (oligosaccharides) of the carbohydrate sequences found in glycoproteins or in glycolipids and one can also use smaller fragments of these sequences, i.e. disaccharide, trisaccharide, tetrasaccharide or a pentasaccharide, because this size usually is sufficient for the oligosaccharide to bind a protein, virus or a cell in a biospecific manner.
- a review or such carbohydrate sequences can be found in e.g. Chemistry and Physics of Lipids, vol. 42, p. 153 -172, 1986, and in Ann. Rev. Biochem., vol. 58, p. 309-350.
- the oligosaccharide is usually modified in the reducing end with an aglycon, which is composed of a glycosidically bound organic group which is suitable for binding to the surface in the biosensor.
- aglycons are OEtSEtCONHNH 2 , - OEtSPhNH2, etc.
- the binding to the surface in the biosensor can be done directly or via a proteins, e.g. bovine serum albumine or via a chemical structure which has been adsorbed or which has been covalently bound to the surface.
- a chemical structure can contain reactive organic groups such as carboxyh sulfonate, cyanate, epoxy-, aldehyde groups or other groups suitable for chemical conjugation with for example an amine or thiol group in the aglycon.
- pathogenic virus or bacteria such as urinary tract bacteria (e.g. P-fimbriated E. coli) or pathogens of the respiratory tract, and bacteria which cause infections/diarrhea in in gastrointestinal tract.
- Non-limiting examples of carbohydrate structures of interest and which can be used in the form of a carbohydrate derivative in a biosensor according to the invention are monosaccharides, disaccharides, trisaccharides and higher oligosaccharides which show biological activity or which has the ability to specfically bind one or more biomolecules or a group of biomolecules.
- biomolecules are other saccharides, peptides and proteins.
- carbohydrate sequences are the blood group determinants (for example A, B, H, Lewis-a, Lewis-b, Lewis-x, Lewis-y), cancer-associated carbohydrate sequences, carbohydrate sequences (often di-, tri- or tetrasaccharides) which bind to pathogenic bacteria ⁇ oxins or virus of for example the respiratory, the gastro ⁇ intestinal or the urinary tract, carbohydrate sequences which bind to proteins/cells/white blood cells associated with inflammatory reactions (for example selectin-carbohydrate reactions).
- blood group determinants for example A, B, H, Lewis-a, Lewis-b, Lewis-x, Lewis-y
- cancer-associated carbohydrate sequences for example the respiratory, the gastro ⁇ intestinal or the urinary tract
- carbohydrate sequences which bind to proteins/cells/white blood cells associated with inflammatory reactions (for example selectin-carbohydrate reactions).
- carbohydrate structures which can be used in a biosensor according to the present invention often contain one or more of the following monosaccharides (or a derivative or an analog of any of these) which are ⁇ - or ⁇ - glycosidically bound: hexosamine, fucose, mannose, glucose, N-acetyl- glucosamine, N-acetyl-galactosamine, xylose, galactose, or another monosaccharide. These components are usually present in for example pyranose or furanose form.
- carbohydrate derivatives are derivatives where the carbohydrate or a derivative or an analog, are modified in the reducing end with an O-, N-, C- or S- glycosidically bound aglycon which can be an alifatic or an aromatic compound, an amino acid-, peptide- or protein molecule or a derivative thereof.
- the aglycon part can thus be composed of for example an 0-, N-, C- or S-glycosidically bound aliphatic or aromatic compound which is bound to an amino acid-, peptide- or protein molecule or a derivative thereof.
- carbohydrate derivatives which can be used according to the invention are structures in which one or more of the hydroxyl groups in the carbohydrate, in addition to or instead of the hydroxyl group in the reducing end of the carbohydrate part, have been modified with an organic or inorganic group. This can be of interest, for example to increase/modify the biological activity or to facilitate the binding to the biosensor surface according to the invention.
- the aglycon part or another group can be used for adsorption or covalent binding of the carbohydrate derivative to the surface of the biosensor and can be used in the invention as a spacer molecule between the biosensor surface and the carbohydrate part to minimise sterical hindrance in the binding of the analyte to the carbohydrate part in the biosensor according to the invention.
- R- consists of an organic compound, for example an alkyl chain of the type (-CH 2 ) n -, in which n is an integer, e.g. in the interval 2 to 8, or is composed of an aromatic group-containing structure
- -X is for example
- Suitable spacer and functional group is chosen by the person skilled in the art and does not limit the scope of the invention.
- the carbohydrate derivative can also, according to the invention, be composed of a natural, in vitro isolated glycoprotein or a recombinant glycoprotein or a glycopeptide.
- This type of derivative can be adsorbed to the surface in the biosensor, for example a gold- or silica surface or another surface which adsorbs proteins, lipids or peptides.
- the carbohydrate derivative is a neoglycoprotein
- This (as for the synthesis of the neoglycoprotein from carbohydrate spacer and protein) can be done with the standard techniques which normally are used for modification of proteins and for immobilisation of proteins to solid supports (see for example methods mentioned in Methods of Enzymology, volumes 44, 102, and 135), and the choice of suitable technology is made by the person skilled in the art in every specific case.
- Examples of methods are coupling or activation of carboxyl groups with carbodiimide reagents, N-hydroxysuccinimide reagents, of hydroxyl groups with CNBr, sulphonyl chloride (tresyl chloride, tosyl chloride), divinyl sulphone, periodate (gives aldehyde groups), thiol groups are activated with thiol reagents of the type SPDP, etc.
- X and Protein can be directly adsorbed on the Biosensor surface above, but between X and Biosensor surface above and between Protein and Biosensor surface above can also a chemical group be present, for example a -CO-CH 2 CH 2 -S- group, i.e. for example:
- protein one can use for example bovine serum albumin, but all for the application suitable types of proteins can be used in the carbohydrate derivative- based biosensor according to the invention.
- biosensor according to the invention can be designed in a variety of configurations. Examples are:
- planar carbohydrate surface which easily can be contacted with the sample, for example a surface designed as a dipstick, this surface can be placed in a measuring device for optical reflectance measurement in air.
- Planar carbohydrate surface which consists of part of the signal transducer which with ease can be brought into contact with the sample for a suitable time, whereafter the sample is removed and the surface of the signal transducer is characterised with a physical measuring method, for example electronic measurement, gravimetric measurement or thermal measurement.
- a physical measuring method for example electronic measurement, gravimetric measurement or thermal measurement.
- the surface of the biosensor can be, for example a gold surface or a modified gold surface, a plastic surface which has been modified with a gold surface, silver surface or another metallic surface, or modifications thereof with polymers to which chemical coupling of carbohydrate can be carried out.
- carbohydrate surfaces which can be used in biosensors according to the invention for binding and analysis/determination of pathogenic bacteria of the urinary tract.
- the thus obtained gold surface modified with digalactoside was dipped for 60 minutes (this time can be varied) in a sample with bacteria of the urinary tract (P-fimbriated E. coli) containing Gal ⁇ l -4Gai-specific receptor protein, followed by rinsing of the surface with distilled water for 2 minutes.
- Another gold surface modified in the same way with Gal ⁇ l -4Gal was dipped in a sample containing another non-infectious E.coli strain which lack the Gal ⁇ l -4Gal-specific receptor protein.
- the extent of binding of the different bacteria to the surfaces was compared with electrom microscopy.
- the bacteria with The Gal ⁇ 1-4Gal-receptor bound to the surface to a ca 10-15 times higher extent than the other bacteria.
- the binding of P-fimbriated E. coli to a gold surface modified with mercapto ⁇ propionic acid alone was ca 20 times lower than to the Gal ⁇ l -4Gal-modified surface.
- Gold plates (not pretreated with mercaptopropionic acid) were immersed in a solution of Gal ⁇ l -4Gal ⁇ -BSA (0.1 mg/ml) in 0.1 M sodium phosphate, pH 6.0, for 1 hour and subsequently immersed in the above BSA solution (3 mg/ml) for 1 minute, rinse with buffer and distilled water and stored as above.
- biosensor surfaces showed similar characteristics and low back-ground binding of bacteria as surface in the first example above.
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9301270 | 1993-04-17 | ||
SE19939301270A SE9301270D0 (en) | 1993-04-19 | 1993-04-19 | BIOSENSOR |
PCT/SE1994/000343 WO1994024561A1 (en) | 1993-04-19 | 1994-04-18 | Immobilized carbohydrate biosensor |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0648333A1 true EP0648333A1 (en) | 1995-04-19 |
EP0648333B1 EP0648333B1 (en) | 2002-01-09 |
Family
ID=20389600
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94914654A Expired - Lifetime EP0648333B1 (en) | 1993-04-17 | 1994-04-18 | Immobilized carbohydrate biosensor |
Country Status (5)
Country | Link |
---|---|
US (4) | US6231733B1 (en) |
EP (1) | EP0648333B1 (en) |
DE (1) | DE69429606T2 (en) |
SE (1) | SE9301270D0 (en) |
WO (1) | WO1994024561A1 (en) |
Families Citing this family (32)
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---|---|---|---|---|
SE9301270D0 (en) | 1993-04-19 | 1993-04-17 | BIOSENSOR | |
JP2001504219A (en) * | 1996-11-11 | 2001-03-27 | ノバルティス アクチェンゲゼルシャフト | Use of biosensors to diagnose plant diseases |
IL120445A0 (en) * | 1997-03-13 | 1997-07-13 | Yissum Res Dev Co | Biosensor for cells |
WO1998049557A1 (en) * | 1997-04-28 | 1998-11-05 | B-E Safe, Inc. | Taxonomic identification of microorganisms, proteins and peptides involved in vertebrate disease states |
JP4163383B2 (en) * | 1998-04-14 | 2008-10-08 | カリフォルニア・インスティテュート・オブ・テクノロジー | Method and system for determining analyte activity |
JP2002526769A (en) | 1998-10-02 | 2002-08-20 | カリフォルニア インスティチュート オブ テクノロジー | Conductive organic sensors, arrays and methods of use |
IL129835A (en) * | 1999-05-06 | 2008-03-20 | Ofer Markman | Polysaccharide sequencing and structure determination |
DE60026309T2 (en) | 1999-05-10 | 2006-12-14 | California Institute Of Technology, Pasadena | USE OF A SPATIAL-TIME REACTION BEHAVIOR IN SENSOR ARRAYS FOR THE DETECTION OF ANALYTES IN FLUIDS |
US7122152B2 (en) | 1999-05-10 | 2006-10-17 | University Of Florida | Spatiotemporal and geometric optimization of sensor arrays for detecting analytes fluids |
AU1861001A (en) * | 1999-11-29 | 2001-06-12 | Syntesome Gesellschaft Fur Medizinische Biochemie Mbh | Arrays of glycan molecules (glycoarrays) on the surface of biochips (glycochips)and uses thereof |
JP2002350447A (en) * | 2001-05-24 | 2002-12-04 | Wako Pure Chem Ind Ltd | Physiological active material fixing carrier, method of manufacturing the same fixing physiological active material, method of analyzing object component in sample and kit for analyzing object component in sample |
US20030087309A1 (en) * | 2001-08-27 | 2003-05-08 | Shiping Chen | Desktop drug screening system |
WO2003021247A1 (en) * | 2001-08-28 | 2003-03-13 | Duke University | Biosensor |
WO2003042697A1 (en) * | 2001-11-14 | 2003-05-22 | Genospectra, Inc. | Biochemical analysis system with combinatorial chemistry applications |
US20030232401A1 (en) * | 2002-06-12 | 2003-12-18 | Pugia Michael J. | Bacterial test method by glycated label binding |
KR101107630B1 (en) * | 2002-10-16 | 2012-01-25 | 듀크 유니버시티 | Biosensor |
GB0225197D0 (en) * | 2002-10-30 | 2002-12-11 | Univ Sheffield | Surface |
US20050287552A1 (en) * | 2003-02-19 | 2005-12-29 | Academia Sinica, Office Of Public Affairs (Technology Transfer) | Carbohydrate encapsulated nanoparticle based affinity mass spectrometry |
US7695738B2 (en) * | 2003-02-19 | 2010-04-13 | Academia Sinica | Carbohydrate encapsulated nanoparticles |
US20040229290A1 (en) * | 2003-05-07 | 2004-11-18 | Duke University | Protein design for receptor-ligand recognition and binding |
JP4009721B2 (en) * | 2003-05-23 | 2007-11-21 | 独立行政法人産業技術総合研究所 | Ion-binding polymer-containing substrate, detection sensor containing the substrate, and pathogen or method for detecting toxins produced by the pathogen |
US20190357827A1 (en) | 2003-08-01 | 2019-11-28 | Dexcom, Inc. | Analyte sensor |
DE602004004753T2 (en) * | 2003-11-28 | 2008-01-31 | C.S.E.M. Centre Suisse D'electronique Et De Microtechnique S.A. | PHOTOLINKER MACROMOLECULES, METALIC SUBSTRATES AND LIGANDS MODIFIED WITH THE LINKERS, AND METHOD FOR THE PRODUCTION THEREOF |
US8532730B2 (en) | 2006-10-04 | 2013-09-10 | Dexcom, Inc. | Analyte sensor |
ES2288429B2 (en) * | 2006-06-28 | 2009-10-13 | Universidad Politecnica De Valencia | CHEMICAL MODIFICATION PROCEDURE OF POLYMER SURFACES INTENDED FOR THE IMMOBILIZATION OF MOLECULES. |
JP5219014B2 (en) * | 2006-10-24 | 2013-06-26 | 独立行政法人科学技術振興機構 | Direct surface immobilization method of saccharide, method of detecting interaction between saccharide and protein |
US8465981B2 (en) * | 2007-08-06 | 2013-06-18 | University Of Kentucky Research Foundation | Polypeptides, systems, and methods useful for detecting glucose |
US20110024043A1 (en) | 2009-07-02 | 2011-02-03 | Dexcom, Inc. | Continuous analyte sensors and methods of making same |
AT509355B1 (en) | 2010-02-10 | 2012-04-15 | Univ Graz Tech | TEST ARRANGEMENT |
DK3575796T3 (en) | 2011-04-15 | 2021-01-18 | Dexcom Inc | ADVANCED ANALYZE SENSOR CALIBRATION AND ERROR DETECTION |
US20170328912A1 (en) * | 2016-05-10 | 2017-11-16 | Regents Of The University Of Minnesota | Glycopolymer capture matrix for use with surface-enhanced raman spectroscopy detection and related systems and methods |
IL252923A0 (en) * | 2017-06-14 | 2017-07-31 | Alon Yasovsky | Sensing system and method for detection of anayltes |
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DE2708018A1 (en) * | 1977-02-24 | 1978-09-07 | Boehringer Mannheim Gmbh | BIOLOGICALLY ACTIVE PROTEIN FIXED TO POLYAMIDE AND THE PROCESS FOR ITS PRODUCTION |
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DE3617763A1 (en) | 1985-05-28 | 1986-12-04 | Olympus Optical Co., Ltd., Tokio/Tokyo | METHOD FOR CARRYING OUT IMMUNOLOGICAL PROVISIONS AND APPARATUS APPARATUS FOR THIS |
EP0215669A3 (en) * | 1985-09-17 | 1989-08-30 | Seiko Instruments Inc. | Analytical device and method for analysis of biochemicals, microbes and cells |
SE451849B (en) | 1985-12-11 | 1987-11-02 | Svenska Sockerfabriks Ab | VIEW TO SYNTHETIZE GYCLOSIDIC BINDINGS AND USE OF THIS RECEIVED PRODUCTS |
JPH0632351B2 (en) * | 1986-05-30 | 1994-04-27 | 日東電工株式会社 | Flexible printed circuit board |
SE466403B (en) | 1988-03-24 | 1992-02-10 | Kurt G I Nilsson | SAID TO SYNTHETIZE Oligosaccharides |
DE3819707A1 (en) * | 1988-06-09 | 1989-12-14 | Max Planck Gesellschaft | METHOD FOR DETERMINING AN ANTIBODY PERTITER |
GB8817710D0 (en) * | 1988-07-25 | 1988-09-01 | Ares Serono Res & Dev Ltd | Method of assay |
SE466521B (en) | 1988-10-03 | 1992-02-24 | Kurt G I Nilsson | REAGENTS OF ANALYZE CONSISTING OF AN ENZYM AND ANOTHER LIGAND, WHICH ARE COVALENTLY BONDED TO A WATER INSULATED PARTICLE WITH A DIAMETER OF LESS THAN 500 AA |
SE465516B (en) | 1989-08-18 | 1991-09-23 | Kurt G I Nilsson | MADE TO MAKE A OLIGOSACCARIDE COMPOUND WHICH GLYCOSIDAS FROM A MOLLUSK IS USED |
GB9009761D0 (en) * | 1990-05-01 | 1990-06-20 | Secr Defence | Substrate regenerating biosensor |
US5082929A (en) * | 1990-08-08 | 1992-01-21 | Bioprobe International, Inc. | Immobilization of glycocompounds and glycoconjugates |
DE4101394A1 (en) * | 1991-01-18 | 1992-07-23 | Medor Lab Fuer Biochemie Und K | METHOD FOR COUPLING CARBOHYDRATES TO CARRIERS, IN PARTICULAR PROTEINS |
SE9102292L (en) | 1991-08-06 | 1993-02-07 | Kurt G I Nilsson | ENZYMATIC METHOD |
WO1994000763A1 (en) | 1992-06-24 | 1994-01-06 | Akzo Nobel N.V. | Method for determining multiple immunocomplexes on one surface using spectroscopy |
SE9301270D0 (en) | 1993-04-19 | 1993-04-17 | BIOSENSOR | |
SE9301677L (en) | 1993-05-14 | 1994-11-18 | Kurt G I Nilsson | synthesis Method |
US5936075A (en) | 1994-05-17 | 1999-08-10 | Bioflexin Ab | Amino-deoxy-disaccharides and amino-deoxy-oligosaccharides |
SE9400034D0 (en) * | 1994-01-06 | 1994-01-06 | Glycorex Ab | Lactose Amine Derivatives |
-
1993
- 1993-04-19 SE SE19939301270A patent/SE9301270D0/en unknown
-
1994
- 1994-04-18 WO PCT/SE1994/000343 patent/WO1994024561A1/en active IP Right Grant
- 1994-04-18 EP EP94914654A patent/EP0648333B1/en not_active Expired - Lifetime
- 1994-04-18 DE DE69429606T patent/DE69429606T2/en not_active Expired - Fee Related
- 1994-12-19 US US08/356,229 patent/US6231733B1/en not_active Expired - Fee Related
-
2001
- 2001-01-23 US US09/766,659 patent/US6887689B2/en not_active Expired - Fee Related
-
2004
- 2004-10-12 US US10/963,095 patent/US7625722B2/en not_active Expired - Fee Related
- 2004-10-12 US US10/962,731 patent/US7244582B1/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO9424561A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20070148635A1 (en) | 2007-06-28 |
SE9301270D0 (en) | 1993-04-17 |
WO1994024561A1 (en) | 1994-10-27 |
DE69429606D1 (en) | 2002-02-14 |
EP0648333B1 (en) | 2002-01-09 |
US7244582B1 (en) | 2007-07-17 |
US20050048583A1 (en) | 2005-03-03 |
DE69429606T2 (en) | 2002-08-14 |
US20010017270A1 (en) | 2001-08-30 |
US6887689B2 (en) | 2005-05-03 |
US7625722B2 (en) | 2009-12-01 |
US6231733B1 (en) | 2001-05-15 |
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